5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydropyrazol-1-carbothioic acid amide | 1022989-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydropyrazol-1-carbothioic acid amide
• 英文别名: 3-phenyl-5-(dimethylaminophenyl)-1-thiocarbamoyl-2-pyrazoline；3-[4-(Dimethylamino)phenyl]-5-phenyl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 1022989-92-9
• 化学式: C₁₈H₂₀N₄S
• 分子量: 324.45
• InChiKey: JYKCBDMBZFRJBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydropyrazol-1-carbothioic acid amide 、 一氯丙酮 以 乙醇 为溶剂， 反应 2.0h， 以86%的产率得到N,N-二甲基-4-[1-(4-甲基-噻唑-2-基)-3-苯基(2-吡唑啉-5-基)]苯胺
  参考文献：
  名称：

  腙酰卤 511 的反应：作为抗菌剂的 5-芳基噻唑和三唑并 [4,3-a] 嘧啶的简便合成

  摘要：

  [5-取代的 2-(3-苯基-5-取代的 2-吡唑啉基)(1,3-噻唑-4-基)]苯基二氮烯、三唑并[3,4-a]嘧啶和 2,3-二氢-1 ,3,4-噻二唑分别由腙酰卤与 5-取代-3-苯基-4,5-二氢吡唑-1-羧基亚胺硫酮酸、嘧啶-2-硫酮、碳二硫酸甲酯反应合成，收率良好。通过元素分析、光谱数据和替代合成方法阐明了新合成化合物的所有结构。新开发的化合物能够极大地抑制细菌（革兰氏阳性和革兰氏阴性）的生长。

  DOI：

  10.1080/10426500701242145
• 作为产物：
  描述：

  苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydropyrazol-1-carbothioic acid amide
  参考文献：
  名称：

  Synthesis, spectroscopic characterization, in vitro cytotoxic and structure activity relationships of some mononuclear Ru(II) complexes

  摘要：

  New mononuclear Ru(II) complexes [Ru(A)(2)(B)](2+), where A=2,2-bipyridine/1,10-phenanthroline and B=3,4,5-tri-OCH3-DPC, 4-CH3-DPC, 4-N(CH3)(2)-DPC, 4-NO2-DPC, N-BITSZ, PTSZ and PINH, were prepared and characterized by spectroscopic methods. The in vitro cytotoxic activities of the complexes and their corresponding ligands were investigated against the human cancer T-lymphocyte cell lines molt 4/c8 and CEM and the murine tumor leukemia cell line L1210, human promyelocytic leukemia cells (HL-60) and Bel-7402 liver cancer cells by MTT assay. The complexes [Ru(A)(2)(B)](2+) (A=1,10-phenanthroline, B=3,4,5-tri-OCH3-DPC) exerts rather more potent activities against all of these cell lines, especially for CEM and L1210. Ru complexes and structure-activity relationships and anticancer mechanisms are also discussed.

  DOI：

  10.1080/00958972.2013.773318

文献信息

• Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Vasylenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1021/jm300789g

  日期：2012.10.25

  The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia

  新型3- [2-（3,5-二芳基-4,5-二氢吡唑-1-基）-4-氧代-4,5-二氢-1,3-噻唑-5-亚烷基的合成及抗肿瘤活性的筛选] -2,3-dihydro-1 H-吲哚-2-ones 1 – 23和3-（3,5-diarylpyrazol-1-yl）-2,3-dihydro-1 H -indol-2-ones 24 –执行39次。美国国家癌症研究所测试了合成化合物的体外抗癌活性。他们中的大多数对白血病，黑素瘤，肺癌，结肠癌，中枢神经系统，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系均表现出抗癌活性。讨论了构效关系。发现最有效的抗癌化合物10具有平均GI 50的活性TGI值分别为0.071μM和0.76μM。它显示出对非小细胞肺癌细胞HOP-92（GI 50 <0.01μM），结肠癌细胞系HCT-116（GI 50 = 0.018μM），CNS癌细胞SNB-75（ GI 50 = 0.0159μM），卵巢癌细胞系NCI
• Induction of Cyp450 enzymes by 4-thiazolidinone-based derivatives in 3T3-L1 cells in vitro
  作者：Konrad A. Szychowski、Bartosz Skóra、Anna Kryshchyshyn-Dylevych、Danylo Kaminskyy、Kamila Rybczyńska-Tkaczyk、Roman Lesyk、Jan Gmiński

  DOI：10.1007/s00210-020-02025-7

  日期：2021.5

  4-Thiazolidinones and related derivatives are regarded as privileged structures in medicinal chemistry and a source of new drug-like compounds. To date it is known that thiazolidinones are able to induce CYP1A1 activity in 3T3-L1 cells. Therefore, to extend the knowledge of the mechanism of thiazolidinones in the cell, four chemically synthesized heterocycles were tested on 3T3-L1 cells. The 3T3-L1 cells were exposed to Les-2194, Les-3640, Les-5935, and Les-6166. Our study showed that 1 μM βNF, Les-2194, and Les-6166 decreased the expression of Ahr mRNA. In turn, βNF, Les-2194, and Les-3640 increased the Cyp1a1 mRNA expression at the same time interval. On the other hand, Les-5935 was found to decrease the Cyp1a1 mRNA expression. Interestingly, the expression of Cyp1a2 mRNA was activated only by βNF and Les-2194. The expression of Cyp1b1 mRNA in the 3T3 cell line increased after the βNF and Les-2194 treatment but declined after the exposure to Les-5935 and Les-6166. Moreover, the Les-2194 and Les-5935 compounds were shown to increase the activity of EROD, MROD, and PROD. Les-3640 increased the activity of EROD and decreased the activity of PROD. In turn, the treatment with Les-6166 resulted in an increase in the activity of EROD and a decrease in the activity of MROD and PROD in the 3T3-L1 cells.

  摘要：4-噻唑烷酮及其相关衍生物被视为药物化学中的特权结构和新药物样化合物的来源。迄今为止已知噻唑烷酮能够诱导3T3-L1细胞中的CYP1A1活性。因此，为了扩展对细胞中噻唑烷酮机制的了解，对3T3-L1细胞进行了四种化学合成的杂环物质的测试。3T3-L1细胞暴露于Les-2194、Les-3640、Les-5935和Les-6166。我们的研究表明，1μM βNF、Les-2194和Les-6166降低了Ahr mRNA的表达。反过来，βNF、Les-2194和Les-3640在同一时间间隔内增加了Cyp1a1 mRNA的表达。另一方面，Les-5935被发现降低了Cyp1a1 mRNA的表达。有趣的是，只有βNF和Les-2194能激活Cyp1a2 mRNA的表达。3T3细胞系中Cyp1b1 mRNA的表达在βNF和Les-2194处理后增加，但在暴露于Les-5935和Les-6166后下降。此外，Les-2194和Les-5935化合物被证明增加了EROD、MROD和PROD的活性。Les-3640增加了EROD的活性并降低了PROD的活性。相反，Les-6166处理导致3T3-L1细胞中EROD活性增加，MROD和PROD活性下降。
• Synthesis and Anticancer and Antiviral Activities of New 2-Pyrazoline-Substituted 4-Thiazolidinones
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Vasylenko、Roman Lesyk

  DOI：10.1002/jhet.1056

  日期：2013.2

  have been synthesized starting from 3-phenyl-5-aryl-1-thiocarbamoyl-2-pyrazolines via [2+3]-cyclization with 2-bromopropionic acid, maleic anhydride, N-arylmaleimides, and aroylacrylic acids. The in vitro anticancer activity of , , , , and were tested by the National Cancer Institute. Compounds , , and demonstrated selective inhibition of leukemia cell lines growth at a single concentration (10−5 M)

  2-（4,5-二氢吡唑-1-基）-噻唑-4-酮（2-5）是通过[2 + 3]从3-苯基-5-芳基-1-硫代氨基甲酰基-2-吡唑啉开始合成的。 -环化与2-溴丙酸，马来酸酐，N-芳基马来酰亚胺和芳酰基丙烯酸。在体外的抗癌活性， ， ， ， 和 由美国国家癌症研究所（National Cancer Institute）测试。化合物， ， 和 证明在单一浓度（10 -5 M）下对白血病细胞系生长的选择性抑制。对多种病毒的抗病毒活性筛选表明，N-（4-甲氧基苯基）-2- 2- [5-（4-甲氧基苯基）-3-苯基-4,5-二氢吡唑-1-基]- 4-氧代-4,5-二氢噻唑-5-基}-乙酰胺 对Tacaribe TRVL 11 573病毒株具有高活性（EC 50 = 0.71μg / mL，选择性指数= 130）。